This song is generally attributed to Dick Burnett, a blind fiddler from Kentucky, who was the first to record it in about 1913, using the name "Farewell Song." However even he was not sure whether he actually wrote the song, saying in an interview many years later, "I think I got the ballad from somebody - I dunno. It may be my song ...". It has been suggested that he adapted it from a Baptist hymn called "Wandering Boy."

Cecil Sharp collected the song in 1918 and published it as "In Old Virginny."

Emry Arthur recorded it in 1928 and Sarah Ogan Gunning rewrote this version as "Girl of Constant Sorrow" in 1936.

The song was popularised by the Stanley Brothers, who recorded it in 1951. Ralph Stanley said in an interview in 2009: "Man of Constant Sorrow" is probably two or three hundred years old. But the first time I heard it when I was y'know, like a small boy, my daddy - my father - he had some of the words to it, and I heard him sing it, and we - my brother and me - we put a few more words to it, and brought it back in existence. I guess if it hadn't been for that it'd have been gone forever. I'm proud to be the one that brought that song back, because I think it's wonderful."

Other notable recordings are by Joan Baez (1960), Judy Collins (1961), Roscoe Holcomb (1961 -- 62), Peter, Paul and Mary (1962), Bob Dylan (1963), Rod Stewart (1969), The Dillards (1972) and Jackson Browne (2000). The song had a new lease of life when performed by the fictitious Soggy Bottom Boys in the movie "O Brother, Where Art Thou?" (2000) in a version based on the Stanley brothers' rendition.